My ex-girlfriend and best buddy is a painter, artist, and is well versed in color theory. She says matching clothes to a person is more about finding certain color shades that match your skin tone/eye color...it's difficult to explain, but if you're ever looking for a new wardrobe, track down an artist versed in color theory. Once you learn what colors compliment you, you'll be making much smarter wardrobe decisions and be saving money.
You should also look for a stylist who can identify your body type, especially if you're in the professional suits world.
Alternatively, if you're a straight guy, track down some gay men for fashion advice. I know it's a bit of a stereotype that gay men magically have a greater fashion sense, but coming fresh out of liberal arts college I can tell you, I've met gay dudes from bro to very feminine, and all of them gave me recommendations on what to wear that was very informative.
I have a broad chest, so I personally like to wear V-neck shirts that emphasize that. I also like polos and plaid/flannel button ups. Not a lot of bald guys look great in a standard collared t-shirt. You also don't want to be wearing clothes that is too "busy." You can pull that off with hair, but shirts that are monocrome or one color are better if you are shaving your head.
But let's take striped polo shirts, a very manly shirt to wear:
1) Horizontal stripes on a bigger guy will emphasis the fact that he's big, that's a no no. For a big dude, you want vertical stripes, and more medium width to the stripes, that will slim him down.
2) Horizontal stripes on a thinner/smaller guy will make him "fill out" and appear to fill his clothes better.
good luck!
